Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living spaces. At the heart of the home is a chef’s kitchen featuring custom cabinetry, high-end appliances, and stylish finishes—perfect for both everyday living and entertaining. The open-concept living and dining areas flow seamlessly, enhanced by updated systems and central air conditioning for year-round comfort. Upstairs, the primary suite provides a serene escape with a spa-like tile bath and soaking tub. Two additional guest bedrooms share a beautifully appointed full bath that also includes convenient laundry. Unique details like a compass rose stained glass window add a distinctive nautical touch. The finished lower level offers even more living space, including a large bedroom—ideal for guests or extended family. Outdoors, a stunning mahogany deck overlooks the newly landscaped backyard, complete with an outdoor shower and perfect areas for entertaining. With close proximity to downtown Vineyard Haven and the beaches of Vineyard Sound, this exceptional home captures the essence of island living—timeless, refined, and move-in ready.
Under contract
$1,999,000
5 Pine Tree Ln, Tisbury, MA 02568
4beds
2,730sqft
Single Family Residence
Built in 1927
7,797 Square Feet Lot
$1,920,500 Zestimate®
$732/sqft
$-- HOA
What's special
Stylish finishesOutdoor showerConvenient laundryNewly landscaped backyardStunning mahogany deckGenerous living spacesUpdated systems
- 391 days |
- 635 |
- 30 |
Zillow last checked:
Listing updated:
Listed by:
Alyssa Halisky,
Wallace & Co. Sotheby's
Source: LINK,MLS#: 43291
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Heat Pump
Appliances
- Included: Stove: Bosch Induction Oven & Stovetop, Washer: Electrolux Front Loading Washer
Features
- AC, Ins, Irr, OSh, Floor 1: See Floor Plans, Floor 2: See Floor Plans
- Flooring: 3
- Basement: Finished lower level with family room and large bedroom. Utility closet.
- Fireplace features: 1
Interior area
- Total structure area: 2,730
- Total interior livable area: 2,730 sqft
Video & virtual tour
Property
Parking
- Parking features: Private driveway
Features
- Exterior features: Deck, Porch, Garden, DdBch, PubBch
- Has view: Yes
- View description: None, Res
- Frontage type: None
Lot
- Size: 7,797 Square Feet
- Features: Newly landscaped yard with back deck
Details
- Additional structures: Outdoor Shower
- Parcel number: TISBM0004FB00000L00001
- Zoning: R25
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: Full foundation with finished basement
Condition
- Year built: 1927
- Major remodel year: 2024
Utilities & green energy
- Sewer: Septic Tank
- Water: Town
- Utilities for property: Cbl
Community & HOA
Location
- Region: Tisbury
Financial & listing details
- Price per square foot: $732/sqft
- Tax assessed value: $1,336,000
- Annual tax amount: $9,913
- Date on market: 5/17/2025
- Listing agreement: E
Estimated market value
$1,920,500
$1.82M - $2.02M
$7,823/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/11/2026 | Contingent | $1,999,000$732/sqft |
Source: LINK #43291 Report a problem | ||
| 2/27/2026 | Price change | $1,999,0000%$732/sqft |
Source: MLS PIN #73480830 Report a problem | ||
| 10/1/2025 | Price change | $1,999,999+0%$733/sqft |
Source: MLS PIN #73410635 Report a problem | ||
| 9/18/2025 | Price change | $1,999,000-8.9%$732/sqft |
Source: Martha's Vineyard MLS #32400203 Report a problem | ||
| 7/15/2025 | Price change | $2,195,000-8.4%$804/sqft |
Source: Martha's Vineyard MLS #32400203 Report a problem | ||
| 5/17/2025 | Listed for sale | $2,395,000-3.8%$877/sqft |
Source: LINK #43291 Report a problem | ||
| 1/31/2025 | Listing removed | $2,490,000$912/sqft |
Source: LINK #42345 Report a problem | ||
| 9/2/2024 | Price change | $2,490,000-3.9%$912/sqft |
Source: Martha's Vineyard MLS #32400203 Report a problem | ||
| 7/31/2024 | Listed for sale | $2,590,000$949/sqft |
Source: LINK #42345 Report a problem | ||
| 7/19/2024 | Listing removed | $2,590,000$949/sqft |
Source: LINK #42204 Report a problem | ||
| 6/24/2024 | Listed for sale | $2,590,000+146.7%$949/sqft |
Source: LINK #42204 Report a problem | ||
| 4/28/2023 | Sold | $1,050,000-4.5%$385/sqft |
Source: LINK #40535 Report a problem | ||
| 3/10/2023 | Pending sale | $1,100,000$403/sqft |
Source: LINK #40535 Report a problem | ||
| 3/2/2023 | Listed for sale | $1,100,000+2100%$403/sqft |
Source: LINK #40535 Report a problem | ||
| 6/3/1998 | Sold | $50,000$18/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,896 -12.7% | $1,043,100 -8% |
| 2024 | $9,044 +7.2% | $1,133,300 -1.6% |
| 2023 | $8,435 +27.1% | $1,152,300 +51% |
| 2022 | $6,638 +2.6% | $762,943 +8.2% |
| 2021 | $6,468 +5% | $705,300 +6.8% |
| 2020 | $6,160 +1.8% | $660,215 +0% |
| 2019 | $6,054 +5.8% | $660,200 +9% |
| 2018 | $5,723 -0.2% | $605,600 -3.8% |
| 2017 | $5,737 +12% | $629,700 +12.6% |
| 2016 | $5,124 +11.1% | $559,400 +8.2% |
| 2015 | $4,610 -4.3% | $516,800 -10% |
| 2014 | $4,818 -0.9% | $574,300 +0.1% |
| 2013 | $4,863 -0.3% | $573,500 -5.8% |
| 2012 | $4,878 +2.2% | $609,000 -4.1% |
| 2011 | $4,774 +9.4% | $634,900 -4.4% |
| 2010 | $4,364 +7% | $664,300 -2.6% |
| 2009 | $4,078 +1.8% | $681,900 -6.5% |
| 2008 | $4,004 +8% | $729,300 +10.7% |
| 2007 | $3,708 +7.7% | $658,600 -0.5% |
| 2006 | $3,442 +2% | $661,900 +15% |
| 2005 | $3,374 +18.2% | $575,700 +63.1% |
| 2004 | $2,855 +4.7% | $352,900 |
| 2003 | $2,728 +5.6% | $352,900 |
| 2002 | $2,583 +4% | $352,900 +89.9% |
| 2000 | $2,484 | $185,800 |
Find assessor info on the county website
Monthly payment
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Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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Climate risks
Neighborhood: 02568
Nearby schools
GreatSchools rating
- 4/10Tisbury Elementary SchoolGrades: PK-8Distance: 1.3 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 3.6 mi
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- Massachusetts
- Dukes County
- Tisbury
- 02568
- 5 Pine Tree Ln






